A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windsor vacation rentals

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

1. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
$852 nightly
The price is $966
Oct 13 - Oct 14
Total with taxes and fees
Wildflower
A swimming pool with lounge chairs and an umbrella, surrounded by a grassy area and trees.

2. Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Healdsburg
9.6 out of 10, Exceptional, (193 reviews)
"Great location and cozy home."
United States
Kelly B.
$878 nightly
The price is $971
Sep 28 - Sep 29
Total with taxes and fees
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

3. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
$979 nightly
The price is $1,101
Sep 28 - Sep 29
Total with taxes and fees
Elegant Vineyard Living at a Private Wine Country Estate
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

4. Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
Eastside Eden - Pool, Hot Tub and Tastings Included
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

5. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (133 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
$98 nightly
The price is $112
Oct 26 - Oct 27
Total with taxes and fees
Wildhaven Sonoma Glamping
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

6. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"Great location!"
United States
Riley F.
$367 nightly
The price is $405
Sep 29 - Sep 30
Total with taxes and fees
Vineyard View Retreat • Fire Pit • Wine Tasting Perks

7. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
$329 nightly
The price is $370
Sep 29 - Sep 30
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

8. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (41 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
$488 nightly
The price is $540
Sep 27 - Sep 28
Total with taxes and fees
Serenity at the Russian River
A deck with outdoor seating, a grill, and a view of a house with large windows.

9. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (36 reviews)
"Great stay, highly recommend!"
United States
Jana P.
$461 nightly
The price is $510
Oct 6 - Oct 7
Total with taxes and fees
Somms Rest ⎮ Designed. Curated. Peaceful.
A living room with a stone fireplace, wooden flooring, a dining area with chairs, and a large window.

10. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
United States
Rachel S.
$485 nightly
The price is $539
Sep 28 - Sep 29
Total with taxes and fees
Wine Country Getaway
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

11. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
$454 nightly
The price is $510
Sep 28 - Sep 29
Total with taxes and fees
Russian River Brew-cation Home
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

12. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
$413 nightly
The price is $459
Sep 28 - Sep 29
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

13. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (79 reviews)
"Lovely vacation rental"
United States
suzanne g.
$373 nightly
The price is $395
Oct 1 - Oct 2
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

14. Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
$299 nightly
The price is $331
Sep 28 - Sep 29
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!
An entrance with a wooden door, a wicker chair, a cushioned bench, a window with a view of trees, and a hanging light fixture.

15. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (53 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
$439 nightly
The price is $485
Sep 27 - Sep 28
Total with taxes and fees
Private Lofted Downtown Studio
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

16. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (76 reviews)
"Our stay was very comfortable."
United States
Kim R.
$606 nightly
The price is $681
Sep 27 - Sep 28
Total with taxes and fees
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A beach with a large rock formation, a sandy shore, and a calm sea.

17. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (66 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
$234 nightly
The price is $251
Oct 18 - Oct 19
Total with taxes and fees
The Tiny Tipsy Turtle
A wooden staircase leading to a building with a balcony, surrounded by trees.

18. Rivers Breeze - Wine Tastings Included

Rivers Breeze - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (20 reviews)
"Lovely place, exactly as described. Really nice place to sit & listen to nature, access to river, well-appointed, easy, and the owners are responsive and easy to work with."
United States
Seppo H.
Rivers Breeze - Wine Tastings Included
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

19. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay!"
United States
Adam C.
$357 nightly
The price is $357
Sep 28 - Sep 29
Total with taxes and fees
Cozy Wine Country Guesthouse with Private Pool & Yard
A covered patio with a dining table, chairs, and a sofa.

20. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
$1,068 nightly
The price is $1,187
Oct 6 - Oct 7
Total with taxes and fees
Redwood Riverfront - Hot Tub and Tastings Included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

The Inn at the Tides

The Inn at the Tides

10/10 Excellent
"We loved our overnight trip to the tides! Enjoyed dinner at restaurant and loved the piano music!"
Bertha 1-night trip
Posted 6 hours ago
The Inn at the Tides

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Powell's Sweet Shoppe - Windsor, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: Visitors like this Windsor vacation home rental. It is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Choose from 30 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Cultural attractions include Pacific Coast Air Museum, whereas Russian River is a spot to enjoy nature. Windsor Golf Club and Windsor Oaks Vineyards are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.